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Pennie began playing drums at the age of 13, and at age 16 decided to pursue music seriously. He spent two years at Berklee College of Music and received a diploma in Music Synthesis, which focuses on electronic music composition and manipulation.

While in high school he was playing in the local New Jersey based band, Prozak. The other 3 members of Prozak were 8 – 10 years Pennie's senior, and in order for Prozak to play the local bars and clubs, Pennie's father would accompany him to the various gigs. Chris played with Prozak from ‘93 until he began attending Berklee School of Music in '95. He recorded ten songs with Prozak during his time with the band but they were never commercially released.

Pennie also spent time with the pop-punk group Boxer. Formed in 1995 with another Berklee graduate, Jeremy McDowell, they became the first band to be signed to the now famous Vagrant Records. They released one album, "The Hurt Process" in 1998, and broke up in late 1999. Pennie also recorded drums for his former tourmates in experimental metalcore group All Else Failed on their 2004 album "This Never Happened". Pennie describes his band, The Dillinger Escape Plan, as being 'mathcore' where they start each song with no structure and an open palette.

As for his role in the Dillinger Escape Plan, he and guitarist Ben Weinman, along with now departed singer and bassist Dimitri Minakakis and Adam Doll respectively, formed the band in March 1997. He and Ben Weinman wrote the majority of Dillinger's material and Pennie called Weinman his "musical soulmate". Pennie also took care of a lot of the electronic influence in the band’s material in the studio as well as onstage, triggering effects and loops with footswitch pedals.

Chris became frustrated with The Dillinger Escape Plan, in particular with Ben Weinman because of a lack of creativity and touring because Weinman was caught up trying to sue somebody. Pennie had previously turned down the Nine Inch Nails job because The Dillinger Escape Plan was 'his baby' but wasn't willing to turn down Coheed and Cambria because of his frustrations with Weinman and subsequently left Dillinger.

On 2 November 2011, Coheed and Cambria announced on their Facebook page that Pennie had left the band.[2] Chris also announced: he had parted ways with Coheed and Cambria, in order to focus on other projects such as Return to Earth and Fight Mannequins.[3]

He has also lent his talent to the predominately electronic band Idiot Pilot on their 2007 released album Wolves. "In addition, the Dillinger Escape Plan's Chris Pennie appears on the album, augmenting several of Wolves' tracks with his drumming prowess. Anderson said the one-two punches of Hoppus, Robinson, Barker, and Pennie are bringing something new to Idiot Pilot's established sound."[4]